Enantioselective total synthesis of isishippuric acid B via intramolecular michael reaction

Munefumi Torihata, Takashi Nakahata, Shigefumi Kuwahara

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The first enantioselective total synthesis of isishippuric acid B bearing a novel 4,5-seco-6-norquadrane skeleton was accomplished from (R)-citronellal with use of a Diels-Alder cycloaddition and an intramolecular Michael addition as the ring-forming steps. Comparison of the optical rotation of the synthetic material with that of the natural product confirmed the absolute configuration of isishippuric acid B to be 1R, 2R, 8R, and 11R.

Original languageEnglish
Pages (from-to)2557-2559
Number of pages3
JournalOrganic letters
Volume9
Issue number13
DOIs
Publication statusPublished - 2007 Jun 21

ASJC Scopus subject areas

  • Molecular Medicine

Fingerprint Dive into the research topics of 'Enantioselective total synthesis of isishippuric acid B via intramolecular michael reaction'. Together they form a unique fingerprint.

  • Cite this